3. Kentucky Derby Quinella Box

The 20 horse Kentucky Derby field makes picking a winner difficult. Bettors must carefully manage risk to profit. Play multiple horses at once with the Quinella Box Bet.

Pick 3 or more horses to finish in the first or second position. Final order doesn’t matter.

Your bet wins if 2 of your selections finish first and second.

Bet loses if one or none of your selections finish top two.

Quinella Box bets cost $2 per combination. The following table lists costs per number of horses boxed.

Quinella Box Costs, $2 Per Combination

Horses

Combinations

Total

3

3

$6

4

6

$12

5

10

$20

6

15

$30

7

21

$42

Tip
Keep Quinella Box to 6 horses or less. Larger quinella boxes are both expensive and inefficient. Consider using an Exacta Wheel bet for 6 or more horses. Key small sets of horses into each finishing position.

Top Kentucky Derby Longshot Winners

1. 2009 Mine That Bird 50 to 1

Jockey: Calvin Borel2009 Kentucky Derby Winner Mine That Bird

Mine that Bird’s 2009 Kentucky Derby win was the most stunning upset in recent memory. He was the second gelding to ever win the derby, just one of nine to ever enter. It seems this unruly horse knew how to run!

A muddy start against a formidable field offered little hope. Then, as the horses broke for home, Mine that Bird surged ahead. He confidently dispatched frontrunners and late closers alike. His final time was 2:02.66, some 6+ lengths ahead of the second finisher.

Jockey Calvin Borel and trainer Bennie Woolley, Jr. were the only two people confident in this horse’s ability. Their beliefs paid off. A $2 bet paid an incredible $103.20.

Mine that Bird later finished second at the Preakness and third at the Belmont Stakes.

2. 2005 Giacomo 50 to 1

Jockey: Mike E. Smith

It was still anyone’s race down the homestretch of Kentucky Derby 131. Afleet Alex, Giacomo and Closing Argument were jockeying for the win. Ultimately Giacomo persevered in the final seventy yards defeating Closing Argument, another 50 to 1 longshot.

This improbable victory has been the only Derby win for both jockey Mike E. Smith and trainer John Shirreffs.

Giacomo’s official time was 2:02.75. He later finished third at the Preakness and seventh at the Belmont Stakes. He came back to win the 2006 San Diego Handicap, then finished fourth in the 2006 Breeders’ Cup Classic.

3. 1940 Gallahadion 36 to 1

Jockey: Carroll Bierman

Bimelech was the odds on favorite at 2 to 5 in the 1940 Kentucky Derby. Few had interest in Gallahadion, owned by the Mars candy company family.

But this 36 to 1 longshot seized the day, driving past Bimelech and Dit at the finish. He clocked a respectable 2:05.00 while time was still being marked in 1/5 seconds.

After a third place Preakness finish, Gallahadion’s luck ran out. He didn’t finish the Belmont Stakes, officially recorded as “unplaced”. Attempts to win subsequent summer races were unsuccessful.

Still, this one hit wonder makes the record books for his incredible win. Jockey Carroll Bierman and trainer Roy Waldron never won another Derby.

4. 1913 Donerail 91 to 1

Jockey: Roscoe Goose

Donerail is the biggest longshot winner of the Kentucky Derby in history. His odds were 91 to 1.

Donerail started slowly and hung with the leaders until the final stretch. There he surged to take the lead. He made his break in the final 1/16 mile leading Ten Point and Gowell to the finish.

His 2:04.8 was a record at the time. Equally impressive was the $184.90 payoff for a $2 Win bet. A Greek man named Elias Dimakos was the prescient and lucky winner.

Donerail started 62 races and won 10 before retiring in 1917. Other notable wins included the Canadian Sportsmen’s Handicap and Hamilton Cup. He appeared once again in 1918 for a turf race but dropped out before the finish.

5. 1999 Charismatic 31 to 1

Jockey: Chris Antley

Perhaps Charismatic should have been a favorite. His pedigree included Secretariat. His jockey was future hall of famer Chris Antley, who won the 1991 Derby riding Strike the Gold. Charismatic’s trainer D. Wayne Lukas had already captured 3 Derby wins. Would 1999 be his 4th?

Running to the finish, it was Cat Thief on the rail with Charismatic charging ahead. Menifee caught up on the outside, attempting to close on both horses. But Charismatic held off both as Menifee’s late surge ran out of track.

Charismatic’s 2:03.20 win cemented the legacies of both Antley and Lukas in horse racing history. He later won the Preakness.

Charismatic’s Triple Crown dreams ended painfully at the Belmont Stakes. He slowed suddenly with about 1/8 mile to go after taking the lead. Jockey Antley eased him up and dismounted, quickly grabbing Charismatic’s front-left leg. A veterinarian determined it was fractured.

Subsequent surgery returned use of the leg. But Charismatic could no longer race. He became a stud until retirement in October 2016. He died in 2017.